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Rapid Synthesis of 3-Methyleneisoindolin-1-ones via Metal-Free Tandem Reactions of Ester-Functionalized Aziridines.
Xing, Siyang; Jin, Changkun; Zhang, Panpan; Yang, Jingmeng; Liang, Yuxia; Ao, Xinglian; Pi, Wenyi; Wang, Kui; Zhu, Bolin.
Afiliación
  • Xing S; Tianjin Key Laboratory of Structure and Performance for Functional Molecules, College of Chemistry, Tianjin Normal University, Tianjin 300387, People's Republic of China.
  • Jin C; Tianjin Key Laboratory of Structure and Performance for Functional Molecules, College of Chemistry, Tianjin Normal University, Tianjin 300387, People's Republic of China.
  • Zhang P; Tianjin Key Laboratory of Structure and Performance for Functional Molecules, College of Chemistry, Tianjin Normal University, Tianjin 300387, People's Republic of China.
  • Yang J; Tianjin Key Laboratory of Structure and Performance for Functional Molecules, College of Chemistry, Tianjin Normal University, Tianjin 300387, People's Republic of China.
  • Liang Y; Tianjin Key Laboratory of Structure and Performance for Functional Molecules, College of Chemistry, Tianjin Normal University, Tianjin 300387, People's Republic of China.
  • Ao X; Tianjin Key Laboratory of Structure and Performance for Functional Molecules, College of Chemistry, Tianjin Normal University, Tianjin 300387, People's Republic of China.
  • Pi W; Tianjin Key Laboratory of Structure and Performance for Functional Molecules, College of Chemistry, Tianjin Normal University, Tianjin 300387, People's Republic of China.
  • Wang K; Tianjin Key Laboratory of Structure and Performance for Functional Molecules, College of Chemistry, Tianjin Normal University, Tianjin 300387, People's Republic of China.
  • Zhu B; Tianjin Key Laboratory of Structure and Performance for Functional Molecules, College of Chemistry, Tianjin Normal University, Tianjin 300387, People's Republic of China.
J Org Chem ; 89(7): 5153-5158, 2024 Apr 05.
Article en En | MEDLINE | ID: mdl-38485493
ABSTRACT
We have disclosed a novel metal-free tandem cyclization reaction for the synthesis of 3-methyleneisoindolin-1-ones starting from ester-functionalized aziridines. This strategy can be effectively promoted by DBU and carboxylic acids. Mechanistically, it involves sequential ring opening of aziridines with carboxylic acids, lactamization, and elimination of carboxylic acids.
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Texto completo: 1 Bases de datos: MEDLINE Idioma: En Revista: J Org Chem Año: 2024 Tipo del documento: Article
Texto completo
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Texto completo: 1 Bases de datos: MEDLINE Idioma: En Revista: J Org Chem Año: 2024 Tipo del documento: Article